(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylammonium benzoate, a versatile building block for chiral 2-aminoalkanols: Concise synthesis and application to nelfinavir, a potent HIV-protease inhibitor

A concise synthesis of a versatile chiral C4 building block for 2-aminoalka nols, (1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethammonium ben zoate (la), was described. 1 (1a and its enantiomer 1b) acted as four stere oisomers of optically active 2-amino-1,3,4-butanetriol. The versatility of I was demonstrated by its application to the practical synthesis of nelfina vir (2), a potent HIV-protease inhibitor, as well as by the stereospecific synthesis of three diastereomers of 2.